Small Group 5-Day Tour Vacation Package in Vermont

Experience Vermont in an Intimate 5-Day Guided Tour

When considering a trip to Vermont, many travelers envision leaf-peeping, charming villages, and unforgettable scenery — all of which this 5-day guided tour hits in spades. With a maximum of just six guests, the experience feels more like traveling with a group of friends than a typical tour bus. We love how this small group setup fosters genuine connections and personalized care, ensuring you won’t feel like just another number.

One standout feature is the tour’s thoughtfully curated itinerary, blending iconic sights with authentic local experiences. From visiting a historic president’s homestead to exploring Vermont’s artisan glass studios, the tour offers a well-rounded taste of the Green Mountain State. However, keep in mind that this is a tightly scheduled adventure; if you prefer a more leisurely pace or spontaneous exploration, some may find it a bit packed.

This tour suits travelers who appreciate a mix of history, scenic beauty, and local culture, all wrapped up in a comfortable, manageable group. Whether you’re a first-timer to Vermont or returning for more, this journey promises both discovery and genuine connections in one of New England’s most picturesque regions.

Key Points

• Intimate Group Size: With only 2 to 6 travelers, expect personalized attention and meaningful interactions.
• Diverse Itinerary: Combines scenic drives, historic sites, and artisan visits for a well-rounded experience.
• Authentic Vermont: Visits iconic spots like the Trapp Family Lodge and local artisans, offering genuine local flavor.
• Expert Guides: Knowledgeable guides, like Natalia, share insider tips and captivating stories.
• Comfortable Transport & Lodging: Air-conditioned vehicle and four nights at Snowed Inn in Killington ensure comfort.
• All Included Attractions: Admission fees are covered, so no surprise costs for key sites.

A Close Look at the Itinerary

Day 1: From Burlington to Stowe and Waterbury

The adventure kicks off early with pickup at your hotel in Burlington, around 9:00 AM. The first day is a delightful blend of scenic drives and tasty stops. You’ll visit Ben & Jerry’s Ice Cream Factory — a must for any sweet tooth — where you can learn about their quirky history and production, plus sample some flavors. Next, Cold Hollow Cider Mill offers an authentic taste of Vermont’s apple harvest, with free samples and a chance to see cider-making in action.

Then comes a visit to the Trapp Family Lodge, famous for inspiring The Sound of Music. This Austrian-style retreat offers stunning views and a glimpse into the family’s history. The day’s highlight is cruising through Smugglers Notch State Park, where winding mountain roads and breathtaking vistas make for great photo opportunities. After exploring Stowe village and grabbing lunch (on your own), the day wraps up with a comfortable drop-off at your Killington hotel.

Day 2: Exploring Woodstock and Quechee

Starting with a scenic drive to Woodstock, Vermont’s quintessential small town, you’ll enjoy a guided tour of the Marsh-Billings-Rockefeller Mansion. Led by a National Park Service ranger, the visit offers insights into its historical significance and the impressive collection of Hudson River School paintings housed there.

Post-tour, you’ll have free time in Woodstock to stroll art galleries, admire historic houses, or cross the iconic covered bridge. Lunch is on your own downtown, giving you a chance to try some local eateries. The afternoon features a visit to Simon Pearce glassblowing studio in Quechee. Watching artisans craft beautiful, handcrafted glassware or pottery is a highlight, and you may even pick up a unique souvenir.

Day 3: The President’s Birthplace and Local Cheese

Day 3 takes you to Plymouth, where you’ll tour the Calvin Coolidge Homestead — a rare chance to see the childhood home of a U.S. president. Plymouth feels like stepping back in time, thanks to its preserved buildings and barns displaying antique tools. The home tour is a meaningful look into Vermont’s contribution to American history.

Near Plymouth, the Plymouth Cheese Factory offers cheese tastings and the chance to buy local cheeses. The focus on Vermont’s dairy traditions makes this stop both tasty and educational. The day’s relaxed pace allows you to appreciate Vermont’s rural charm.

Day 4: Montpelier, Warren, and Vermont’s Natural Beauty

This day begins with a guided tour of Montpelier’s State House, one of the oldest and best-preserved in the country. The guide provides fascinating insights into Vermont’s political history and architecture.

Afterward, the scenic drive along Vermont RT 100 guides you through some of Vermont’s most stunning natural landscapes. Highlights include Appalachian Gap, offering sweeping views, and Moss Glen Falls, a photogenic waterfall that’s perfect for quick photos or just soaking in the scenery. Lunch at the Warren Store introduces you to classic Vermont fare, in a setting that feels like stepping into a local’s kitchen.

Day 5: Shelburne’s Art and Agriculture

Your final day focuses on arts, culture, and farm life. The Shelburne Museum is a sprawling collection of historic buildings, art, and artifacts. The Steamboat Ticonderoga, a National Historic Landmark, offers a glimpse into Vermont’s maritime history, with its detailed interior recreations.

Following the museum, Shelburne Farms offers a peaceful farm-to-table experience, emphasizing Vermont’s agricultural roots and sustainable practices. The self-guided visit allows you to explore at your own pace, taking in the views of the farm and surrounding landscape.

What We Loved Most

Knowledgeable Guides: Multiple reviews highlight guides like Natalia for their warmth, passion, and insider knowledge. Travelers appreciate guides who go beyond surface facts, sharing stories and local lore that truly bring the experience alive.

Stunning Vistas & Authentic Spots: From mountain passes to artisan studios, the tour offers a rich mix of Vermont’s natural beauty and genuine local culture. The scenic drives along VT RT 100, in particular, are consistently praised.

Well-Curated Experiences: The stops are carefully chosen to showcase Vermont’s highlights while offering authentic interactions, whether tasting cheese, watching glassblowing, or exploring historic sites.

Value for Money: While the cost is $2,495 per person, reviews suggest the inclusion of attractions, comfortable transportation, and four nights of lodging make this a worthwhile investment for a comprehensive Vermont experience.

Considerations

Some travelers note the tour can be quite packed, especially if you prefer a slower pace or spontaneous exploration. The schedule is tightly managed, which is great for seeing everything, but might feel hurried for those wanting more leisure time. Also, gratuities for guides are not included, so budget accordingly if you want to tip well.

Final Thoughts: Who Is This Tour Perfect For?

This small-group 5-day Vermont tour is ideal for travelers who crave an organized yet intimate experience, blending scenic drives, cultural sites, and local artisans. It’s a great choice for first-time visitors who want a guided overview without the stress of planning, but also for seasoned Vermont fans eager to uncover hidden gems with a knowledgeable guide.

If you value authenticity, comfort, and a well-rounded itinerary, this tour delivers. It’s especially suited for those who enjoy learning about local history, tasting regional products, and making new friends along the way. The limited group size ensures personalized attention, making it a memorable way to experience Vermont’s beauty and charm.

FAQ

What is included in the tour price?
The tour includes transportation in an air-conditioned vehicle, four nights at Snowed Inn in Killington, a continental breakfast each morning, and admission fees to all attractions visited.

Are meals included?
No, lunch and dinner are not included, but there are plenty of nearby restaurants for you to choose from each day.

What if I need a double bed?
If two beds are required in one room, it’s best to inquire before booking to ensure availability and arrangements.

How many people will be on the tour?
The tour accommodates a minimum of 2 and a maximum of 6 travelers, creating an intimate group environment.

What should I do if I arrive late or need to cancel?
Since the booking is non-refundable and cannot be changed, make sure to arrive on time. Arrivals in Burlington should be the night before the tour starts.

Is this tour suitable for children or seniors?
Most travelers can participate, but given the schedule and walking involved, it’s best for those who are reasonably mobile and comfortable with a somewhat full itinerary.

How long is each day’s drive?
Most days involve about 7 hours of activities and sightseeing, with some driving between locations. Comfortable transportation and scenic routes make this manageable.

What are the highlights I shouldn’t miss?
Expect to love the scenic mountain drives, the historic sites like Plymouth and Woodstock, and the artisan experiences at glass studios and farms.

Can I extend my stay after the tour?
Absolutely. Many travelers choose to stay longer in Vermont to explore more of what the state has to offer, especially in charming towns like Burlington or Stowe.

This 5-day Vermont tour offers a beautifully balanced mix of scenic beauty, cultural exploration, and authentic local experiences, all within a cozy, small-group setting that makes Vermont feel like your own secret getaway.